US20060165734A1 - Novel method of deodorization for fat odor and composition obtained by the same - Google Patents

Novel method of deodorization for fat odor and composition obtained by the same Download PDF

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Publication number
US20060165734A1
US20060165734A1 US10/548,805 US54880505A US2006165734A1 US 20060165734 A1 US20060165734 A1 US 20060165734A1 US 54880505 A US54880505 A US 54880505A US 2006165734 A1 US2006165734 A1 US 2006165734A1
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acid
fatty acid
highly unsaturated
unsaturated fatty
omega
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Kyoko Konishi
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Suntory Ltd
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Suntory Ltd
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Publication of US20060165734A1 publication Critical patent/US20060165734A1/en
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B5/00—Preserving by using additives, e.g. anti-oxidants
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
    • A23L5/20—Removal of unwanted matter, e.g. deodorisation or detoxification
    • A23L5/27—Removal of unwanted matter, e.g. deodorisation or detoxification by chemical treatment, by adsorption or by absorption
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

Definitions

  • the present invention relates to a novel deodorizing method, for oily odors, comprising the combining of a carotenoid and an oil comprised of a highly unsaturated fatty acid or compound having for a constituent fatty acid a highly unsaturated fatty acid and, more particularly, at least one compound selected from the group consisting of an alcohol ester of a highly unsaturated fatty acid, a triglyceride having for a constituent fatty acid a highly unsaturated fatty acid, and a phospholipid having for a constituent fatty acid a highly unsaturated fatty acid, and to a composition on which a novel deodorization method has been practiced.
  • the pathway by which highly unsaturated fatty acids are biosynthesized in humans consists of two representative systems, namely the omega-3 system and the omega-6 system (omega indicates the number of carbon atoms to the carbon atom where the first double bond is located counting from the terminal methyl group of a fatty acid).
  • omega-6 highly unsaturated fatty acids include linoleic acid, ⁇ -linolenic acid, dihomo- ⁇ -linolenic acid and arachidonic acid
  • omega-3 highly unsaturated fatty acids include ⁇ -linolenic acid, eicosapentaenoic acid and docosahexaenoic acid.
  • fatty acids are involved in regulation of membrane fluidity, as major constituents of cell membranes, with arachidonic acid, for example, accounting for roughly 10% of the fatty acids that compose important organs such as the blood and liver (for example, the composite ratios of fatty acids in phospholipids of human blood consist of 11% arachidonic acid, 1% eicosapentaenoic acid and 3% docosahexaenoic acid) and, while they exhibit various functions related to the body's metabolism, they also fulfill the important role of being direct precursors of prostaglandins.
  • arachidonic acid for example, accounting for roughly 10% of the fatty acids that compose important organs such as the blood and liver (for example, the composite ratios of fatty acids in phospholipids of human blood consist of 11% arachidonic acid, 1% eicosapentaenoic acid and 3% docosahexaenoic acid) and, while they exhibit various functions related to the body's metabolism, they also fulfill the important role of
  • arachidonic acid As a nutrient of newborns and infants and as a constituent fatty acid of intrinsic cannabinoids (2-arachidonoyl monoglycerol, anandamide) demonstrating neuroactivating action.
  • Arachidonic acid and compounds having arachidonic acid as a constituent fatty acid were also recently clearly demonstrated to prevent decreases in learning ability accompanying aging by the administration of arachidonic acid, and/or compounds having arachidonic acid as a constituent fatty acid, to aged rats subjected to a Morris water maze test as reported in Japanese Unexamined Patent Publication No. 2003-48831 entitled, “Composition having Preventive or Ameliorative Action on Symptoms or Diseases Caused by Decreased Brain Function”.
  • omega-3 highly unsaturated fatty acids of eicosapentaenoic acid (abbreviated as EPA) and docosahexaenoic acid (abbreviated as DHA) are known to have numerous physiological functions, including preventive effects on lifestyle diseases such as arteriosclerosis and thrombosis, carcinostatic action and learning ability enhancement action, and attempts are being made to use them in pharmaceuticals, special health foods and so forth.
  • Omega-6 highly unsaturated fatty acids are biosynthesized in the body by using linoleic acid as a precursor, while omega-3 highly unsaturated fatty acids are similarly biosynthesized using ⁇ -linolenic acid as a precursor.
  • humans are unable to biosynthesize linoleic acid and ⁇ -linolenic acid, in the case of, for example, omega-6 highly unsaturated fatty acids using linoleic acid as a precursor, they are converted to ⁇ -linolenic acid, dihomo- ⁇ -linolenic acid and arachidonic acid after ingesting plant foods and repeatedly desaturating and elongating the carbon chain.
  • arachidonic acid, EPA and DHA are normally adequately biosynthesized if foods rich in linoleic acid and ⁇ -linolenic acid are ingested.
  • these highly unsaturated fatty acids tend to be deficient, thereby making it desirable that they be ingested directly as oil or fat.
  • Highly unsaturated fatty acids are fatty acids that have 18 or more carbon atoms and 2 or more double bonds, and are easily auto-oxidized resulting in the generation of an oxidation odor.
  • Typical known examples of methods based on a deodorizing principle include: (1) adsorption (activated charcoal, zeolite), (2) dissolution (deodorizing agent such as silica gel), (3) degradation (biodegradation, oxidative degradation (ozone O 3 ), hydrolysis (photocatalyst OH ⁇ ), ionic degradation (oxygen cluster ions) or combustion (oxidative catalysis, direct combustion)), and (4) coagulation (removal by surrounding with a high molecular weight compound).
  • Patent Document 1 Japanese Unexamined Patent
  • the present invention relates to a novel deodorizing method for oily odors comprising the combining of a carotenoid and an oil comprised of a highly unsaturated fatty acid or compound having for a constituent fatty acid a highly unsaturated fatty acid, and more particularly, at least one compound selected from the group consisting of an alcohol ester of a highly unsaturated fatty acid, a triglyceride having for a constituent fatty acid a highly unsaturated fatty acid, and a phospholipid having for a constituent fatty acid a highly unsaturated fatty acid, and to a composition on which a novel deodorization method has been practiced.
  • an object of the present invention is to provide a novel deodorizing method for oily odors comprising combining a carotenoid with a highly unsaturated fatty acid or compound having for a constituent fatty acid a highly unsaturated fatty acid, and more particularly, at least one compound selected from the group consisting of an alcohol ester of a highly unsaturated fatty acid, a triglyceride having for a constituent fatty acid a highly unsaturated fatty acid and a phospholipid having for a constituent fatty acid a highly unsaturated fatty acid, and a composition on which novel deodorization has been implemented.
  • the present invention provides a composition on which a novel deodorizing method for oily odors has been implemented that contains a carotenoid in an oil. Moreover, the present invention provides a novel deodorizing method for oily odors comprising adding a carotenoid to an oil.
  • the oil is preferably a highly unsaturated fatty acid or compound containing as a constituent fatty acid a highly unsaturated fatty acid, examples of which include an alcohol ester of a highly unsaturated fatty acid, a triglyceride having as a constituent fatty acid a highly unsaturated fatty acid, and a phospholipid having as a constituent fatty acid a highly unsaturated fatty acid.
  • the aforementioned highly unsaturated fatty acid is, for example, an omega-6 highly unsaturated fatty acid and/or an omega-3 highly unsaturated fatty acid and/or an omega-9 highly unsaturated fatty acid.
  • omega-6 highly unsaturated fatty acid examples include 9,12-octadecadienoic acid (linoleic acid) 18:2 ⁇ 6,6,9,12-octadecatrienoic acid ( ⁇ -linolenic acid) 18:3 ⁇ 6,8,11,14-eicosatrienoic acid (dihomo- ⁇ -linolenic acid) 20:3 ⁇ 6,5,8,11,14-eicosatetraenoic acid (arachidonic acid) 20:4 ⁇ 6,7,10,13,16-docosatetraenoic acid 22:4 ⁇ 6 and 4,7,10,13,16-docosapentaenoic acid 22:5 ⁇ 6, examples of the aforementioned omega-3 highly unsaturated fatty acid include 9,12,15-octadecatrienoic acid ( ⁇ -linolenic acid) 18:3 ⁇ 3,6,9,12,15-octadecatetraenoic acid (stearidonic acid) 18:4 ⁇
  • a triglyceride having for a constituent fatty acid an omega-6 highly unsaturated fatty acid is extracted from microbial cells obtained by culturing a microbe belonging to the genus Mortierella, for example.
  • An example of the aforementioned triglyceride having for a constituent an omega-3 highly unsaturated fatty acid is fish oil.
  • carotenoids examples include carotenes or xanthophylls such as ⁇ -carotene, ⁇ -carotene, ⁇ -cryptoxanthin, ⁇ -cryptoxanthin, ⁇ -carotene, lycopene, lutein, fucoxanthin, capsanthin, zeaxanthin, phytofluene, phytoene, canthaxanthin and astaxanthin.
  • the ratio of carotenoid to highly unsaturated fatty acid that composes the oil is preferably 0.00001 to 0.1, for example 0.0001 to 0.01, and more preferably 0.001 to 0.01.
  • the aforementioned composition is, for example, a functional food, nutritional supplement food, special health food or geriatric food.
  • the present invention relates to a novel deodorizing method for oily odors comprising the combining of a carotenoid and an oil comprised of a highly unsaturated fatty acid or compound having for a constituent fatty acid a highly unsaturated fatty acid, and more particularly, at least one compound selected from the group consisting of an alcohol ester of a highly unsaturated fatty acid, a triglyceride having for a constituent fatty acid a highly unsaturated fatty acid, and a phospholipid having for a constituent fatty acid a highly unsaturated fatty acid, and to a composition on which a novel deodorization method has been practiced.
  • a highly unsaturated fatty acid or compound having for a constituent fatty acid a highly unsaturated fatty acid can be used for the target oil of the present invention.
  • Highly unsaturated fatty acids indicate a fatty acid having 18 or more carbon atoms and 2 or more double bonds, examples of which include omega-6 highly unsaturated fatty acids such as 9,12-octadecadienoic acid (linoleic acid) 18:2 ⁇ 6,6,9,12-octadecatrienoic acid ( ⁇ -linolenic acid) 18:3 ⁇ 6,8,11,14-eicosatrienoic acid (dihomo- ⁇ -linolenic acid) 20:3 ⁇ 6,5,8,11,14-eicosatetraenoic acid (arachidonic acid) 20:4 ⁇ 6,7,10,13,16-docosatetraenoic acid 22:4 ⁇ 6 and 4,7,10,13,16-docosapentaenoic acid 22:5 ⁇ 6.
  • omega-3 highly unsaturated fatty acids include 9,12,15-octadecatrienoic acid ( ⁇ -linolenic acid) 18:3 ⁇ 3,6,9,12,15-octadecatetraenoic acid (stearidonic acid) 18:4 ⁇ 3,11,14,17-eicosatrienoic acid (dihomo- ⁇ -linolenic acid) 20:3 ⁇ 3,8,11,14,17-eicosatetraenoic acid 20:4 ⁇ 3,5,8,11,14,17-eicosapentaenoic acid 20:5 ⁇ 3, 7,10,13,16,19-docosapentaenoic acid 22:5 ⁇ 3 and 4,7,10,13,16,19-docosahexaenoic acid 22:6 ⁇ 3.
  • omega-9 highly unsaturated fatty acids examples include 6,9-octadecadienoic acid 18:2 ⁇ 9, 8,11-eicosadienoic acid 20:2 ⁇ 9 and 5,8,11-eicosatrienoic acid (Mead acid) 20:3 ⁇ 9.
  • the highly unsaturated fatty acid is arachidonic acid
  • all compounds having arachidonic acid as a constituent fatty acid can be used.
  • Examples of compounds having arachidonic acid as a constituent fatty acid include calcium salts, sodium salts and other salts of arachidonic acid.
  • other examples of the aforementioned compounds include lower alcohol esters of arachidonic acid such as arachidonic methyl ester and arachidonic ethyl ester.
  • triglycerides, phospholipids and glycolipids having arachidonic acid as a constituent fatty acid can also be used.
  • the present invention is not limited to the aforementioned examples, and all compounds having arachidonic acid as a constituent fatty acid can be used.
  • triglycerides are particularly desirable for the form of the oil.
  • triglycerides containing arachidonic acid can already be obtained industrially, and can be supplied as edible oils.
  • a triglyceride containing triglyceride in which all or a portion of the constituent fatty acids is arachidonic acid can be used for an oil of the present invention.
  • an oil (triglyceride) containing arachidonic acid In order to use an oil (triglyceride) containing arachidonic acid industrially, a microbe having the ability to produce arachidonic acid can be cultured, and oil can then be extracted from the resulting microbial cells.
  • microbes having the ability to produce oil (triglyceride) having arachidonic acid as a constituent fatty acid include microbes belonging to the genuses Mortierella, Conidiobolus, Pythium, Phytophthora, Penicillium, Cladosporium, Mucor, Fusarium, Aspergillus, Rhodotorula, Entomophthora, Echinosporangium and Saprolegnia.
  • microbes belonging to the genus Mortierella include Mortierella elongata, Mortierella exigua, Mortierella hygrophila and Mortierella alpina.
  • strains examples include Mortierella elongata IFO8570 , Mortierella exigua IFO8571 , Mortierella hygrophila IFO5941 and Mortierella alpina IFO8568, ATCC16266, ATCC32221, ATCC42430, CBS219.35, CBS224.37, CBS250.53, CBS343.66, CBS527.72, CBS529.72, CBS608.70 and CBS754.68.
  • the spores or mycelia of that microbial strain are cultured by inoculating into a liquid or solid medium.
  • a liquid medium although typically used carbon sources such as glucose, fructose, xylose, saccharose, maltose, soluble starch, molasses, glycerol or mannitol can be used for the carbon source, the carbon source is not limited to these.
  • nitrogen sources examples include organic nitrogen sources such as yeast extract, malt extract, beef extract, casamino acids, corn stiplica, soybean protein, defatted soybeans, cottonseed residue and other naturally-occurring nitrogen sources, as well as inorganic nitrogen sources such as sodium nitrate, ammonium nitrate and ammonium sulfate.
  • organic nitrogen sources such as yeast extract, malt extract, beef extract, casamino acids, corn stiplica, soybean protein, defatted soybeans, cottonseed residue and other naturally-occurring nitrogen sources
  • inorganic nitrogen sources such as sodium nitrate, ammonium nitrate and ammonium sulfate.
  • Trace nutrients including inorganic salts such as phosphates, magnesium sulfate, iron sulfate and copper sulfate as well as vitamins can also be used as necessary. There are no particular restrictions on the concentrations of these medium components provided they do not inhibit microbial growth.
  • the concentration of the carbon source should be 0.1 to 40% by weight, and preferably 1 to 25% by weight.
  • the starting amount of nitrogen source added is typically 0.1 to 10% by weight and preferably 0.1 to 6% by weight, and the nitrogen source may be added during the course of culturing.
  • an oil (triglyceride) having an arachidonic acid content of 45% or more can be produced and used as an oil by controlling the concentration of carbon source in the medium.
  • a specific example of culturing consists of a microbial growth period during the 2nd to 4th day of culturing followed by an oil accumulation period starting after the 2nd to 4th day of culturing.
  • the starting concentration of the carbon source should typically be 1 to 8% by weight and preferably 1 to 4% by weight, the carbon source should be added gradually only between the microbial growth period and the first part of the oil accumulation period, and the total amount of the gradually-added carbon source should be 2 to 20% and preferably 5 to 15%.
  • the amount of the carbon source gradually added between the microbial growth period and first part of the oil accumulation period should be such that the carbon source is added corresponding to the starting concentration of the nitrogen source and then added so that the carbon source concentration in the medium reaches zero starting on day 7 of culturing, preferably starting on day 6 of culturing, and more preferably starting on day 4 of culturing.
  • the culturing temperature of microbes having the ability to produce an oil (triglyceride) having arachidonic acid as a constituent fatty acid is 5 to 40° C. and preferably 20 to 30° C.
  • highly unsaturated fatty acid can be produced by continuing culturing at 5 to 20° C. after growing the microbes by culturing at 20 to 30° C.
  • the ratio of highly unsaturated fatty acid to the total fatty acids produced can also be increased by controlling the temperature in this manner.
  • the pH of the medium is 4 to 10 and preferably 5 to 9, and culturing is carried out by fermentation with aeration and agitation, shaking culture or static culture. Culturing is normally carried out for 2 to 30 days, preferably 5 to 20 days and more preferably 5 to 15 days.
  • an oil (triglyceride) having for a constituent fatty acid dihomo- ⁇ -linolenic acid or an omega-9 highly unsaturated fatty acid can be used as a target oil of the present invention.
  • a method has previously been developed for efficiently producing oil (triglyceride) having dihomo- ⁇ -linolenic acid as a constituent fatty acid (Japanese Patent No. 3354581).
  • an oil having for a constituent fatty acid an omega-3 highly unsaturated fatty acid can also be provided as a target oil of the present invention.
  • oils include tuna oil, sardine oil, bonito oil, cod oil and linseed oil.
  • oils can also be used that have been obtained by culturing a microbe capable of efficiently producing oil having an omega-3 highly unsaturated fatty acid as a constituent fatty acid and extracting the resulting oil.
  • microbes capable of producing oils having an omega-3 highly unsaturated fatty acid as a constituent fatty acid include those belonging to the genuses Crypthecodenium, Thraustochytrium, Schizochytrium, Ulkenia, Japonochytrium and Haliphthoros.
  • An oily odor can be decreased, alleviated or deodorized by combining a carotenoid with a highly unsaturated fatty acid or compound having for a constituent fatty acid a highly unsaturated fatty acid, and more particularly, at least one compound selected from the group consisting of an alcohol ester of a highly unsaturated fatty acid, a triglyceride having for a constituent fatty acid a highly unsaturated fatty acid, and a phospholipid having for a constituent fatty acid a highly unsaturated fatty acid.
  • carotenoids include ⁇ -carotene, ⁇ -carotene, ⁇ -cryptoxanthin, ⁇ -cryptoxanthin, ⁇ -carotene, lycopene, lutein, fucoxanthin, capsanthin, zeaxanthin, phytofluene, phytoene, canthaxanthin and astaxanthin.
  • the blending ratio of carotenoid required for deodorizing the oily odor is 0.00001 to 0.1, preferably 0.0001 to 0.01 and more preferably 0.001 to 0.01, as the ratio of carotenoid to the total amount of highly unsaturated fatty acid that composes the oil.
  • a highly unsaturated fatty acid or compound having a highly unsaturated fatty acid as a constituent fatty acid and more particularly, an alcohol ester of a highly unsaturated fatty acid, triglyceride having as a constituent fatty acid a highly unsaturated fatty acid and phospholipid having as a constituent fatty acid a highly unsaturated fatty acid, and these can be used as raw materials or additives of foods, beverages, cosmetics and pharmaceuticals. There are no restrictions whatsoever on their purpose of use or amount used.
  • Examples of food compositions include general foods as well as functional foods, nutritional supplement foods, premature infant formulas, baby formulas, baby foods, foods for pregnant women and geriatric foods.
  • foods that contain oil include naturally-occurring foods that inherently contain oils such as meat, fish and nuts, foods to which oils are added during cooking such as soup, foods that use oil as a heating medium such as doughnuts, oily foods such as butter, processed foods to which oil is added during processing such as cookies, and foods on which oil is sprayed or coated during finishing processing such as hard biscuits.
  • oils can also be added to agricultural product foods, fermented foods, livestock products, marine products or beverages which do not contain oil.
  • the aforementioned applications may also be in the form of functional foods or pharmaceuticals, examples of which include processed forms such as enteral nutritional preparations, powders, granules, troches, internal medicines, suspensions, emulsions and syrups.
  • a control oil was prepared by mixing 64% by weight of an oil (triglyceride) containing 25% arachidonic acid as a constituent fatty acid and 36% by weight of a purified fish oil (triglyceride) containing 46% DHA as a constituent fatty acid. Astaxanthin and other pigments were added to the control oil at the concentrations shown in Table 1 to prepare five types of sample oils. The deodorizing effects on the odor were assessed by 15 panelists in the form of a sensory test. The odors of the sample oils were evaluated to one of five grades based on the following standards while assigning a score of 0 to the odor of the control oil.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Polymers & Plastics (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Food Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nutrition Science (AREA)
  • Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
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  • Fats And Perfumes (AREA)
  • Edible Oils And Fats (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
US10/548,805 2003-06-09 2004-06-08 Novel method of deodorization for fat odor and composition obtained by the same Abandoned US20060165734A1 (en)

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JP2003163598 2003-06-09
JP2003-163598 2003-06-09
PCT/JP2004/008284 WO2004108870A1 (ja) 2003-06-09 2004-06-08 油脂臭の新規脱臭法及びその組成物

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EP (1) EP1632556A4 (ko)
JP (1) JPWO2004108870A1 (ko)
KR (1) KR20060037237A (ko)
CN (1) CN1761736A (ko)
AU (1) AU2004245844A1 (ko)
CA (1) CA2517661A1 (ko)
TW (1) TW200503635A (ko)
WO (1) WO2004108870A1 (ko)

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CN111690464A (zh) * 2019-03-15 2020-09-22 王征 Dha藻油、鱼油去腥方法
WO2021010491A1 (en) * 2019-07-16 2021-01-21 The Nisshin Oillio Group, Ltd. Method for manufacturing refined edible oil and/or fat, method for improving light exposure odor of edible oil and/or fat, and refined edible oil and/or fat
JP2022533470A (ja) * 2019-07-16 2022-07-22 日清オイリオグループ株式会社 精製食用油脂の製造方法、食用油脂の曝光臭改善方法、及び精製食用油脂
JP7180031B2 (ja) 2019-07-16 2022-11-29 日清オイリオグループ株式会社 精製食用油脂の製造方法、食用油脂の曝光臭改善方法、及び精製食用油脂

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EP1632556A4 (en) 2006-12-20
CN1761736A (zh) 2006-04-19
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